Spirocyclic rhodamine B benzoisothiazole derivative: a multi-stimuli fluorescent switch manifesting ethanol-responsiveness, photo responsiveness, and acidochromism

Battula, Himabindu; Nath, Moromi; Mishra, Sabyashachi; Jayanty, Subbalakshmi

doi:10.1039/d2ra08022b

Cited by 4 publications

(2 citation statements)

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“…Due to the deficit π-conjugation, spirocyclic lactam derivatives are restricted for most of the biological labeling experiments; [8] yet, prospectively used as molecular chemosensors for detecting heavy metal ions (Hg 2 + , Sn 2 + , Pb 2 + , Fe 3 + , and Al 3 + ), [9] sensing aromatic acids in drugs and environmental samples. [10] The open-chain RHB derivatives comprise extended π-electron conjugation and show comprehensive signals in absorption and fluorescence spectroscopy. Hence, rhodamine derivatives are widely used in fluorescence microscopy to stain cell compartments mostly in mitochondria, [11][12] besides becoming a better choice as labeling agents in the light of fluorescence response and ease of synthesis and functionalization.…”

Section: Introductionmentioning

confidence: 99%

“…RHB derivatives basically exist in two forms i. e., open chain form (highly fluorescent, pink) and spirocyclic form (non‐fluorescent, colorless). Due to the deficit π‐conjugation, spirocyclic lactam derivatives are restricted for most of the biological labeling experiments; [8] yet, prospectively used as molecular chemosensors for detecting heavy metal ions (Hg 2+ , Sn 2+ , Pb 2+ , Fe 3+ , and Al 3+ ), [9] sensing aromatic acids in drugs and environmental samples [10] . The open‐chain RHB derivatives comprise extended π‐electron conjugation and show comprehensive signals in absorption and fluorescence spectroscopy.…”

Section: Introductionmentioning

confidence: 99%

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Rhodamine B Amide Derivatives with Anticancer Activity and Fluorescence Properties for Potential Theranostic Applications

Battula,

Reddy Bollareddy,

Vamsi Krishna Venuganti

et al. 2024

ChemistrySelect

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Rhodamine B (RHB) based derivatives are especially known for their dye characteristics. Nevertheless, very limited of such revealed promising in‐vivo and in‐vitro therapeutic potency; besides demonstrating great interest due to their excellent photophysical and structural proficiency. Therefore, novel RHB derivatives with significant biological activity are requisite. Hence, current work presents the contemporary design aspect, synthesis, characterization, and anticancer activity of five new RHB amides attained by reacting RHB specifically with simple small amines being side chains of existing anticancer drugs. Therefore, this strategy resulted in a dual effect i. e. fluorescence property and considerable anticancer activity among achieved RHB amides. Obtained fluorophores exhibited emission wavelength at ∼560 nm, a fluorescence quantum yield Φf=10 to 40 % in aqueous solutions, and showed operational stability in pH 4–10, conditions. Further, a study for in‐vitro cell‐based experiments was carried out, wherein AGS (Human gastric cancer) and B16F10 (Murine melanoma) cells were used to screen the compounds. Hydroxy phenyl piperazine substituted RHB amide showed greater growth inhibition than other compounds with an IC50 value of 1.18 μM and 9.07 μM in AGS and B16F10 cells. Fluorescence imaging was performed for the compounds in AGS cells with DAPI as the counterstain using confocal laser microscopy.

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